2-溴苯腈 → 4-[(2'-Cyanobiphenyl-4-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline

HRID 5681

反应方程式

HRID 5681 反应方程式
[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2].Br[C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[C:27]#[N:28]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:11]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[N:4]=[C:3]([CH2:1][CH3:2])[CH:12]=2)=[CH:16][CH:17]=1)#[N:28]

参与物

6

反应物 2

HCID 162722-溴苯腈HCID 151714224-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid

产物 1

HCID 197964084-[(2'-Cyanobiphenyl-4-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline收率 49.4%

试剂、催化剂与溶剂 3

HCID 178418397HCID 178418397，化合物催化剂HCID 1140甲苯溶剂HCID 10340Carbonic acid sodium salt (1:2)溶剂

实验过程

Tetrakis(triphenylphosphine)palladium (40 mg) was added to a suspension of 4-[(2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]-phenylboronic acid (200 mg) and 2-bromobenzonitrile (106 mg) in toluene (2 ml) ethanol (0.5 ml) and 2M aqueous sodium carbonate (0.58 ml). The mixture was degassed and placed under an atmosphere of argon, then heated under reflux for 12 hours. The resulting solution was cooled to ambient temperature, and dichloromethane (30 ml) and water (10 ml) were added. The organic layer was separated, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (3:1 v/v), and the product triturated with ether/hexane to give 4-[(2'-cyanobiphenyl-4-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline (106 mg) as a white solid, m.p. 147°-148° C.; NMR (CDCl3): 1.29(t,3H), 1.7-1.95(m,4H), 5.17(s,2H), 6.57(s,1H), 7.4-7.7 (complex m,7 H), 7.78(d,1H); mass spectrum (+ve CI) 369 (M+H)+.

后处理

  1. customThe mixture was degassed
  2. temperatureheated
  3. temperatureunder reflux for 12 hours
  4. additiondichloromethane (30 ml) and water (10 ml) were added
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate/hexane (3:1 v/v)
  10. customthe product triturated with ether/hexane

来源与证据

ORD记录
ord-f2e47c7899134a9295da63016e60ddb0
来源数据集
uspto-grants-1993_09
专利号
US05245035

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